Vacation Rentals in Fairfield, CT

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Fairfield, CT holiday rentals
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355 Holiday rentals and Airbnb in Fairfield, CT

Best family friendly Fairfield, CT holiday rentals

Among the 355 accommodations in Fairfield, CT, here are the 4 best family friendly rentals

Renovated 3br Apt / Easy Check-in / Familyfriendly - Fairfield, CT
No reviews

Renovated 3br Apt / Easy Check-in / Familyfriendly

apartment, Bridgeport
This three-bedroom Bridgeport West Side apartment, near the Adventure Park at Discovery Museum and South Benson Marina, offers convenient access to Bridgeport's attractions.
The 84 square metre self-catering flat sleeps eight, boasting a fully equipped kitchen, high-speed internet, smart TVs, and a shared garden; self check-in is available.
The Elijah Sterling House - Fairfield, CT
10 66 reviews

The Elijah Sterling House

apartment, Trumbull
This three-bedroom apartment is situated in Trumbull, Connecticut, a 10-minute drive from the Total Mortgage Arena and the Bridgeport Amphitheatre.
The apartment, housed in the historic Elijah Sterling House, dating back to 1791, offers a fully equipped kitchen, a spacious outdoor patio, and multiple living areas, accommodating up to seven guests.
Southport Shoreline Charm: Elegant Coastal Escape - Fairfield, CT
8.8 5 reviews

Southport Shoreline Charm: Elegant Coastal Escape

apartment, Fairfield
This three-bedroom flat is conveniently located in Southport, Fairfield, just a short 5-minute drive from the beaches and a few minutes from the town centre. The surrounding area offers a range of shops, restaurants, and attractions, making it an ideal base for exploring the local area.
The property features a spacious living area, dining room, and a cosy back room with a large flat-screen TV. It can comfortably accommodate up to seven guests. The apartment is fully equipped with everything you need for a comfortable stay, including a kitchen with a dishwasher, a washing machine, and a dryer, plus a ping pong table in the basement for entertainment.
Charming Colonial For Events!  Perfect For Family Reunions And Group Getaways! - Fairfield, CT
8.8 10 reviews

Charming Colonial For Events! Perfect For Family Reunions And Group Getaways!

apartment, Bridgeport
This six-bedroom, four-bathroom house, situated in Bridgeport's Downtown South Historic District near Perry House, offers easy access to attractions such as Beardsley Zoo and the Bridgeport Bluefish Baseball Club (distances not specified).
The 3,300 sq ft (approximately 307 sq m) property sleeps 8-12 guests and includes a modern master suite with a private terrace, a den, stainless steel appliances, off-street parking for six cars, and extensive outdoor space including a half-acre lawn.

Best Fairfield, CT holiday rentals with a pool

Among the 355 accommodations in Fairfield, CT, here are the 4 best rentals with a pool

Home In Fairfield - Fairfield, CT
9.8 13 reviews

Home In Fairfield

apartment, Fairfield
This modern house is located in Fairfield, just a short distance from the town centre and a kilometre from the freeway exit and Metro North station. The area is quiet and residential, with easy access to shops, restaurants and amenities.
This five-bedroom property can comfortably accommodate up to ten guests. The house includes a fully equipped kitchen, a spacious living area, a private garden and a swimming pool. Guests can enjoy a range of amenities, including a fitness centre, a games room, a barbecue area and a mudroom with direct access to the pool.
Fairfield! 5 Bedroom, 3.5 Bath On Cul-de-sac - Fairfield, CT
10 52 reviews

Fairfield! 5 Bedroom, 3.5 Bath On Cul-de-sac

apartment, Fairfield
This spacious, renovated apartment in Fairfield is conveniently located just a short distance from the town centre, universities, and transportation to NYC Grand Central. The apartment boasts excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The apartment has 5 bedrooms and 3 bathrooms, comfortably accommodating up to 12 guests. Amenities include a private heated pool, a well-equipped kitchen, a spacious living area, a family room with a large TV, and a fully furnished garden with outdoor furniture.
Bright Zen Studio - Fairfield, CT
9.2 30 reviews

Bright Zen Studio

apartment, Fairfield
This Fairfield apartment is located on a quiet historic street, just a block away from the lively Post Road, offering easy access to shops, restaurants and the town centre. The property has received excellent ratings for its cleanliness, location and overall experience.
The home is spacious and designed to evoke a relaxed beach atmosphere. Guests can enjoy outdoor dining by the pool, relax in the garden, and make use of the fully equipped kitchen, which includes a dishwasher, fridge, freezer and microwave.
Characterful Iconic Weston Lodge. - Fairfield, CT
No reviews

Characterful Iconic Weston Lodge.

apartment, Weston
This tranquil four-bedroom flat, offering a unique getaway experience, is located in a peaceful residential area of Weston, a short distance from the town centre and its shops and restaurants.
This spacious accommodation for six guests boasts air conditioning, a swimming pool, jacuzzi, garden, and parking, with a kitchen equipped with a fridge and dishwasher.

Frequently asked questions about holiday rentals in Fairfield, CT

  • What are the must-see sights in Fairfield, Connecticut?

    Fairfield boasts a lovely mix of historical sites and natural beauty. You definitely want to check out the Fairfield Museum and History Center to learn about the town's rich past. Lake Mohegan is gorgeous for a stroll or picnic, and the charming downtown area offers plenty of boutique shopping and places to grab a bite to eat. The historic Old Town Hall is also worth a visit.
  • What are the best Airbnb and holiday rentals in Fairfield, CT?

    The Inn At Fairfield Beach, Southport - Ct Across From Beach and Cozy Home Away From Home are the most popular Airbnb and holiday rentals in Fairfield, CT among travellers.

  • Are there any unique natural phenomena in Fairfield, Connecticut?

    Fairfield doesn't have any dramatic, unique natural phenomena like geysers or massive caves. However, its location on Long Island Sound provides beautiful coastal scenery, and the diverse ecosystems within Lake Mohegan and the surrounding areas offer opportunities for birdwatching and nature walks. The beaches are also a key attraction.
  • What are the most popular Airbnbs in Fairfield, CT?

  • What essentials should you bring along to Fairfield, Connecticut?

    Pack comfortable walking shoes, as you'll likely be doing a lot of exploring on foot. Depending on the time of year, bring layers of clothing as the weather can be unpredictable. Sunscreen and insect repellent are always good ideas, especially during the warmer months. Don't forget your swimwear if you plan on hitting the beach!
  • What are the best holiday rentals with a pool in Fairfield, CT?

  • What famous events or festivals are happening in Fairfield, Connecticut?

    Fairfield hosts various local events throughout the year. Information on specific dates and events is best found closer to your travel dates by checking the town's official website or local event listings. There isn't one single, nationally renowned festival that defines Fairfield.
  • What are the best rentals for families and kids in Fairfield, CT?

  • Where can you find the best restaurants serving local dishes in Fairfield, Connecticut, and what are the must-try specialties?

    Fairfield has a diverse culinary scene. For fresh seafood, try one of the restaurants along the coast. There are also many excellent Italian restaurants reflecting the area's heritage. Specific restaurant recommendations change frequently, so checking local reviews closer to your visit is recommended. There isn't one single 'must-try' Fairfield specialty, but the emphasis is on fresh, local ingredients.
  • What are the best rentals or Airbnbs with a jacuzzi in Fairfield, CT?

  • What are some less-famous attractions in Fairfield, Connecticut that are worth a visit?

    The Pequotsepos Nature Center offers lovely nature trails and educational exhibits. Exploring the various smaller parks and beaches scattered throughout town can also be a rewarding experience. Many of Fairfield's residential areas have beautiful architecture and charming streets to wander.
  • What are the best activities for engaging with locals and understanding their culture in Fairfield, Connecticut?

    Visiting local farmers' markets is a great way to interact with residents and sample local produce. Attending community events or local festivals (check local listings for schedules) can also provide opportunities to meet people. Simply striking up conversations with people in local shops or cafes is another way to experience the local culture.
  • What unique natural landscapes and terrain features can travellers explore in Fairfield, Connecticut?

    Fairfield's landscape is characterised by its coastal location, with beaches and the Long Island Sound. Inland, you'll find rolling hills, wetlands, and several smaller lakes and ponds, including Lake Mohegan. The terrain is generally fairly flat, making it easy to explore on foot or by bicycle.
  • How many days are ideal for a visit to Fairfield, Connecticut, and what are some itinerary suggestions?

    Two to three days is a good amount of time to explore Fairfield's main attractions. A possible itinerary could include: Day 1: Explore downtown, visit the Fairfield Museum and History Center, enjoy a meal by the water. Day 2: Spend time at Lake Mohegan, relax on the beach, and explore one of the smaller parks. Day 3: Visit the Pequotsepos Nature Center and perhaps take a scenic drive along the coast.

Nearby regions

Best Fairfield, CT holiday rentals with a balcony

2-bedroom Modern Apartment For Relaxing Stays - Fairfield, CT
No reviews

2-bedroom Modern Apartment For Relaxing Stays

apartment, Bridgeport
This two-bedroom flat is situated in Bridgeport's West End - West Side, offering convenient access to Silver Sands State Park and The Coastal Centre at Milford Point, with Beardsley Zoo and the Regina A. Quick Centre for the Arts also within proximity.
This accommodation for four guests boasts air conditioning, a balcony, and parking, with nearby attractions including the Hartford HealthCare Amphitheatre and Total Mortgage Arena, making it ideal for exploring local events and natural beauty.
Villa Après Sea - Fairfield, CT
9.0 1 review

Villa Après Sea

house, Westport
This Westport holiday home offers exclusive private access to Compo Beach, located 27 kilometres from Silver Sands State Park and 32 kilometres from Connecticut Post Mall.
This spacious, air-conditioned detached house covers 305 square metres, accommodating up to 11 guests with four bathrooms, a fully equipped kitchen, complimentary Wi-Fi, and free private parking.
Beechmont-charming Colonial For Events And Getaways! - Fairfield, CT
8.0 1 review

Beechmont-charming Colonial For Events And Getaways!

house, Bridgeport
This Bridgeport property, a colonial-style house, is located 13.7km from Silver Sands State Park and 19.3km from the Connecticut Post Mall, offering convenient access to local attractions.
The 307 square metre dwelling boasts one bedroom, four bathrooms, and accommodates up to 23 guests, featuring a fully equipped kitchen, free Wi-Fi, private parking, and a terrace/garden.

Best Fairfield, CT holiday rentals with parking

Modern Artist Retreat Near Beach - Fairfield, CT
9.3 47 reviews

Modern Artist Retreat Near Beach

apartment, Fairfield
This Fairfield apartment is conveniently located just a short walk from the beach, shops, historical sites, and a wide selection of restaurants. With excellent user, location, and cleanliness ratings, this property offers a comfortable and enjoyable stay.
The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, air conditioning, a private garden, a swimming pool, a jacuzzi bath, and a separate in-law suite option available for an extra fee.
Lake Hills Suite - Fairfield, CT
10 35 reviews

Lake Hills Suite

apartment, Fairfield
This modern one-bedroom apartment is situated in Fairfield's Lake Hills area, offering convenient proximity to local universities, restaurants, and shops.
The self-contained suite features a queen-size bed, a queen-size sofa bed, a fully equipped kitchenette, in-unit laundry, and dedicated parking, comfortably accommodating up to four guests.
2 Bdrm Walk To Beach And Town - Fairfield, CT
10 2 reviews

2 Bdrm Walk To Beach And Town

apartment, Fairfield
This modern townhouse in Fairfield is situated a short walk from the town's shopping and dining areas, public transport links including the train station, and the beach.
This two-bedroom, two-bathroom flat accommodates up to six guests and features air conditioning, a fully equipped kitchen with a dishwasher, and on-site laundry facilities.
Cozy Family Home On Quiet Street - Fairfield, CT
9.7 49 reviews

Cozy Family Home On Quiet Street

apartment, Fairfield
This two-bedroom flat is located in the Fairfield Beach district, approximately 1.6 kilometres from town beaches and a ten-minute drive from outdoor recreation.
This newly remodelled residence accommodates up to four guests and features a fully equipped eat-in kitchen with GE appliances, a three-season porch, a fenced yard, WiFi, and a gas BBQ grill.
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